Dimethylamine → HCID 12610525, compound

HRID 1622065Notes

Reaction equation

HRID 1622065 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[CH3:15][NH:16][CH3:17]>O1CCCC1.C(OCC)(=O)C>[CH3:15][N:16]([CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 13789512-Bromo-1-dodecanol

Product 1

HCID 12610525HCID 12610525, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 12-bromo-1-dodecanol (1 g, 3.8 mmoles) in anhydrous tetrahydrofuran (10 mL) was treated with a 2.0 M solution of dimethylamine in tetrahydrofuran (10 mL). The reaction was stirred at room temperature for 3 days. TLC analysis on silica using 25% ethyl acetate, 75% hexanes as eluent showed the formation of a polar product with little starting material. The reaction was diluted with ethyl acetate (75 mL) and washed twice with aqueous sodium bicarbonate and water. The ethyl acetate solution was then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Yield=1.2 g (wax). TLC analysis on silica (25% methanol, 75% ethyl acetate) showed a streaking product with Rf ˜0.1. This product 4a, was used without purification.

Workup

  1. washwashed twice with aqueous sodium bicarbonate and water
  2. dry with materialThe ethyl acetate solution was then dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThis product 4a, was used without purification

Sources & evidence

ORD record
ord-e2eba349d41d4efa8a7158d34ea8ce98
Source dataset
uspto-grants-2014_07
Patent number
US08778624B2

Reaction notes

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